17438-14-1

Basic information

• Product Name: dimethyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate
• Synonyms: dimethyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate;3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-, dimethyl est er;1,4-Dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid dimethyl ester;2,6-Dimethyl-1,4-dihydro-3,5-pyridinedicarboxylic acid dimethyl ester;Einecs 241-458-3;2,6-Dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylicaciddimethylester
• CAS NO: 17438-14-1
• Molecular Formula: C₁₁H₁₅NO₄
• Molecular Weight: 225.2411
• EINECS: 241-458-3
• Mol File: 17438-14-1.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 321.9°Cat760mmHg
• Flash Point: 148.5°C
• Appearance: /
• Density: 1.147g/cm³
• Vapor Pressure: 0.000289mmHg at 25°C
• Refractive Index: 1.491
• CAS DataBase Reference: dimethyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate(17438-14-1)
• EPA Substance Registry System: dimethyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate(17438-14-1)

Safety Data

• Hazardous Substances Data: 17438-14-1(Hazardous Substances Data)

Usage

Uses

Dimethyl 2,6-Dimethyl-1,4-dihydropyridine-3,5-dicarboxylate is used in method for synthesizing 3,4-dihydropyrimidinone compound by asymmetric transfer hydrogenation.

InChI:InChI=1/C11H15NO4/c1-6-8(10(13)15-3)5-9(7(2)12-6)11(14)16-4/h12H,5H2,1-4H3

Upstream product

• 100-97-0 hexamethylenetetramine 
• 105-45-3 acetoacetic acid methyl ester 
• 124-38-9 carbon dioxide 
• 50-00-0 formaldehyd 
• 78-84-2 isobutyraldehyde 
• 21731-17-9 methyl 3-aminocrotonate 

Downstream Products

• 27525-74-2 dimethyl 2,6-dimethylpyridine-3,5-dicarboxylate 

Relevant articles and documents

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1,4-Dihydropyridine/BF3OEt2 for the reduction of imines: Influences of the amount of added BF3OEt2 and the substitution at N-1 and C-4 of the dihydropyridine ring

We have evaluated four 1,4-dihydropyridines (DHPs 1a, 1b, 1c and 1d) as reducing agents, which presented free (hydrogenated) or phenyl-substituted N-1 and C-4 positions of the DHP ring. Reactions combining each of the DHP and different amounts of BF3OEt2 were evaluated for the reduction of imine 2a (N-benzylideneaniline). DHP simultaneously substituted at N-1 and C-4 (1a), and DHP substituted at C-4 (1b) gave lower yields for reduction of 2a in comparison with DHPs 1c and 1d (both unsubstituted at the C-4 position). By evaluating the amount of added BF3OEt2 to the reaction mixture, we have found that DHP 1c (substituted at N-1) provided its best yield for amine 3a (82%) when associated with stoichiometric amounts BF3OEt2, while DHP 1d (N-1- and C-4-unsubstituted derivative) was more effective (90% yield) with catalytic quantities of the Lewis acid. The reaction system using DHP 1c under stoichiometric BF3OEt2 could also be successfully applied with additional imine examples and under reductive amination conditions.

Donor–Acceptor Complex Enables Alkoxyl Radical Generation for Metal-Free C(sp3)–C(sp3) Cleavage and Allylation/Alkenylation

The alkoxyl radical is an essential and prevalent reactive intermediate for chemical and biological studies. Here we report the first donor–acceptor complex-enabled alkoxyl radical generation under metal-free reaction conditions induced by visible light. Hantzsch ester forms the key donor–acceptor complex with N-alkoxyl derivatives, which is elucidated by a series of spectrometry and mechanistic experiments. Selective C(sp3)-C(sp3) bond cleavage and allylation/alkenylation is demonstrated for the first time using this photocatalyst-free approach with linear primary, secondary, and tertiary alkoxyl radicals.